Ethyl chloroformate → HCID 59139899, compound

HRID 1799474Notes

Reaction equation

HRID 1799474 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([C:14](O)=[O:15])=[N:10][N:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:24](=[O:26])[CH3:25])[CH:18]=3)[C:8]2=[O:27])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.ClC(OCC)=O.[BH4-].[Na+]>C1COCC1.O>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([CH2:14][OH:15])=[N:10][N:9]([C:17]3[CH:18]=[C:19]([NH:23][C:24](=[O:26])[CH3:25])[CH:20]=[CH:21][CH:22]=3)[C:8]2=[O:27])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 4311764Sodium borohydrideHCID 68699892HCID 68699892, compound

Product 1

HCID 59139899HCID 59139899, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

According to Scheme 7 Step 5: To a solution of 11(D) (380 mg, 0.92 mmol),) and diisopropylethylamine (189 μL, 1.1 mmol) in THF (10 mL) at 0° C. under nitrogen atmosphere was added ethyl chloroformate (101 μL, 1.06 mmol) dropwise. The reaction mixture was stirred for 1 h then treated dropwise with a solution of sodium borohydride (90 mg, 2.38 mmol) in water (2 mL). The mixture was stirred overnight at room temperature and quenched slowly with a saturated solution of NaHCO3 (100 mL). The aqueous layer was extracted thrice with CH2Cl2 (100 mL). The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure to afford a yellow solid. The crude solid was purified by flash chromatography with silica gel (Merck Flashmart prepacked column 20 g SiO2) using CH2Cl2/MeOH 97/3 as eluant to afford N-(3-(4-(4-chlorobenzyl)-6-(hydroxymethyl)-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide 11(E) (32 mg, 9%) as a white solid.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. customquenched slowly with a saturated solution of NaHCO3 (100 mL)
  3. extractionThe aqueous layer was extracted thrice with CH2Cl2 (100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford a yellow solid
  8. customThe crude solid was purified by flash chromatography with silica gel (Merck Flashmart prepacked column 20 g SiO2)

Sources & evidence

ORD record
ord-e3d86581ccd34d7dbe975d6fb3bca090
Source dataset
uspto-grants-2013_01
Patent number
US08344138B2

Reaction notes

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